GB735112A - Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof - Google Patents
Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereofInfo
- Publication number
- GB735112A GB735112A GB10742/52A GB1074252A GB735112A GB 735112 A GB735112 A GB 735112A GB 10742/52 A GB10742/52 A GB 10742/52A GB 1074252 A GB1074252 A GB 1074252A GB 735112 A GB735112 A GB 735112A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- tetrahydro
- aliphatic amino
- formyl
- amino acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises the calcium salts of 5,6,7,8-tetrahydro-N5-formyl pteroic acid and aliphatic amino acid amides thereof, and a process for the preparation thereof by reacting 5,6,7,8-tetrahydro-N5-formyl pteroic acid or an aliphatic amino acid amide thereof with an inorganic calcium compound in an aqueous medium, or by treating 5,6,7,8-tetrahydro-N10-formyl pteroic acid or 5,6,7,8-tetrahydro-N5, N10-diformyl pteroic acid or an aliphatic amino acid amide thereof with aqueous sodium hydroxide whereby a soluble sodium salt is formed in an alkaline solution, heating and subsequently acidifying the reaction mixture to form 5,6,7,8-tetrahydro - N5 - formyl pteroic acid or an aliphatic amino acid amide thereof, and then reacting the said acid or acid amide with an inorganic calcium compound in an aqueous medium at a pH within the range of 7 to 14, e.g. 10 to 13, to produce the required calcium salt. The heating to form the N5-formyl compound may be carried out at 80 DEG to 100 DEG C. The inorganic calcium compound may be calcium chloride in which case the resulting reaction mixture is diluted with a water-miscible organic solvent to precipitate the required calcium salt. The aliphatic amino acid amide group may be derived from glutamic or aspartic acid or glycine, leucine, alanine, isovaline or cysteine. In the example calcium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamate is prepared by the methods outlined above and also be adding calcium sulphate to barium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamic acid in an aqueous media. Specifications 733,062 and 733,130 are referred to. N5,N10 - Diformylpteroic acid and aliphatic amino acid amides thereof are prepared by reacting pteroic acid or an aliphatic amino acid amide thereof with 98 to 100 per cent formic acid-preferably in the presence of acetic anhydride. Barium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamic acid is prepared by reacting pteroylglutamic acid and formic acid to form N10 - formylpteroylglutamic acid, hydrogenating the product in the presence of platinum oxide to form p 5,6,7,8-tetrahydro-N10-formylpteroylglutamic acid which is then heated at an alkaline pH to form the corresponding N5-formyl compound and aqueous barium chloride is added to precipitate impurity, the required barium salt being precipitated by adding alcohol to the clear solution.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US735112XA | 1951-05-05 | 1951-05-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB735112A true GB735112A (en) | 1955-08-17 |
Family
ID=22114119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10742/52A Expired GB735112A (en) | 1951-05-05 | 1952-04-29 | Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB735112A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2927113A (en) * | 1957-10-14 | 1960-03-01 | Lepetit Spa | Leucovorin purification |
EP0548895A2 (en) * | 1991-12-21 | 1993-06-30 | Sapec S.A. Fine Chemicals | Process for the preparation of pure diasteroisomers of tetrahydrofolates |
-
1952
- 1952-04-29 GB GB10742/52A patent/GB735112A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2927113A (en) * | 1957-10-14 | 1960-03-01 | Lepetit Spa | Leucovorin purification |
EP0548895A2 (en) * | 1991-12-21 | 1993-06-30 | Sapec S.A. Fine Chemicals | Process for the preparation of pure diasteroisomers of tetrahydrofolates |
EP0548895A3 (en) * | 1991-12-21 | 1993-08-11 | Sapec S.A. Fine Chemicals | Process for the preparation of pure diasteroisomers of tetrahydrofolates |
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